title: Total synthesis and biological activity of natural product Urukthapelstatin A.
abstract: Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly, several intermediates, including the linear and serine cyclized precursors, show a 100-fold decrease in cytotoxicity, with IC50's in the low micromolar range. These data indicate that the rigidity and the consecutive aromatic heterocyclic system are responsible for the biological activity.
authors.affiliation: Department of Chemistry and Biochemistry, 5500 Campanile Drive, San Diego State University, San Diego, California 92182-1030, USA.
authors.forename: Chun-Chieh
authors.initials: CC
authors.lastname: Lin
authors.forename: Worawan
authors.initials: W
authors.lastname: Tantisantisom
authors.forename: Shelli R
authors.initials: SR
authors.lastname: McAlpine
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D020128:Inhibitory Concentration 50; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001688:Biological Products; D013844:Thiazoles; C521435:urukthapelstatin A; D012694:Serine; D007930:Leucine